December 16th 2007

You can't make a list about Tony Romo and not include something about Jessica Simpson can you?

Well, December 16, 2007 was the first time in which Simpson showed up at a Cowboys game wearing her pink Romo jersey.

Romo threw three interceptions that day and had a 22.2 QB rating for the game, and the Cowboys lost to the Eagles 10-6, starting the spread of the idea that having Simpson at football games left Romo distracted, and negatively impacted his performance.

Draft Day

He was a three time All-American and three time OVC Player of the Year.

He then went to the combine and wowed quite a few scouts, with many teams showing interest in the young fella, alas, when draft day came, he did not hear his name called.

In hindsight, that might have been one of the best things that could have happen to Romo, as he was contacted and signed by the Cowboys, plus, it sounds better to be the undrafted quarterback who worked his way up the ranks, rather than a sixth or seventh round pick.

Cabo With Jessica

Romo and Simpson were photographed in Cabo San Lucas during the bye week of the 2008 playoffs, the week before he and the Cowboys lost in a close game with the Giants.

Romo was heartily criticized by the media for being so lax on his preparations, saying that it sends a bad message to the rest of the team to vacation during the season.

Even Cowboy great Troy Aikman said, "I think maybe things happened so quickly for Tony in terms of obscurity to all of a sudden national spotlight that he hasn't fully grasped what being the Cowboys quarterback is all about."

2008 Week 17 Vs. Eagles

In the eleventh hour, Romo and the Cowboys faced off against the Eagles for the final playoff spot available in the NFC.

The Cowboys went on to get trounced 44-6, as Romo threw an interception and lost two fumbles.

He passed for only 186 yards and no touchdowns and his record in December fell to 5-8 in his career at that point. This raised questions of his ability to be a good quarterback and leader in the clutch.

Cowboys Stadium Opener

In the home opener of the 2009 season, the first home game played in Jerry Jones' palace, Romo and the Cowboys laid an egg.

He threw three interceptions against only one touchdown and 127 yards passing.

The loss led to many questioning his performance in big games, such as Tony Dorsett, who said, "Well, for one thing, I don't know why on God's earth Tony Romo has been anointed a superstar in the National Football League,"

The Fumble

It is the absolute worst thing that a player can do, make a mistake that costs his team the game, and this was one of those mistakes.

The field goal would have sent the Cowboys to the second round of the playoffs.

The thing about this play is, that if Romo would have made it those last few inches and scored a touchdown, we would be talking about that play completely differently. It would be a testament to Romo's quick mind rather than his nervous fumble.